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An awkward situation

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In midlife dating, we sometimes encounter situations that are just too awkward to have a ready-made answer. I remember one from early in my dating re-entry. I wish I could forget it. I’m not sure I would have an easy answer if it happened again.

The gentleman and I were dating a few months and neither of us were exploring dating others, not because of any overt exclusivity discussion. More because we were busy and not unhappy with the relationship, although I wouldn’t say I was happy either. It was a relationship of convenience — at least for me.

We saw each other at least once on the weekend and once during the week. At first he paid for all dinners, and I’d pay for the movie or after-dinner drink or dessert on the way home. Then I stepped up and took turns treating for dinners, too. Although at the time, my divorce had taken a major economic toll on my life. When my ex left, my expenses doubled immediately and my income went down dramatically as I just couldn’t market my services with much gusto.

So when it was my turn to treat, I’d suggest a modest restaurant. When it was his turn, he nearly always chose an upscale one, as he liked wine and fancy meals. Not that I mind those, but he was more insistent about them than me.

One day he asked, “Would you like to go to the Peobo Bryson/James Ingram concert?” I like those artists, but not so much that I would drive the hour to see them and pay a high ticket price. But my beau liked me to accompany him to events like this, so I said yes. He made an attempt to buy the tickets online, but couldn’t complete the transaction. He called me: “I have a client call in 3 minutes and I can’t complete the online transaction. The concert is almost sold out. Can you go online and get the tickets?” What was I to say? I said yes.

The tickets cost more than I would have spent considering my economic situation. I assumed he would pay me back, although he never said he would. When we arrived at the event, he suggested I go to will call while he parked the car. If I did this, I’d miss the opportunity for him to say to the box office, “Can we put this on my credit card?” So I said I’d wait for him at will call while he parked. When he arrived, we asked the clerk for our tickets. Since I’d already paid for them, there was no discussion of payment.

I’m a tad embarrassed to share that as I sat through the concert, I couldn’t shake dwelling on the high cost of the tickets. And I wasn’t enjoying the show that much — probably because I was obsessing about the cost of the tickets.

I felt uncouth and chintzy to bring up the reimbursement for the tickets, so I said nothing. My guy knew I was barely scraping by. How could he not know that this expenditure was more than I’d have volunteered to take on? I stewed and fretted.

It never came up. He was generous to me in some ways, so I justified that I was evening up the score. But I couldn’t shake that if I were going to treat for a high-cost event, it would have been for an artist for whom I was a big fan, not just sort of liked. I felt a little duped to treat for an evening I would have never offered to spring for.

This same man had earlier suggested we go to Paris together for vacation. I told him that my finances could not support such a holiday and perhaps we should wait until I could split the costs. He said he understood my situation and would pay for everything if I would use my frequent flyer points to get us business class tickets. So it wasn’t as if he didn’t know my situation. (We ended up not going because we couldn’t get tickets that fit our schedules.)

The tit and tat of finances during dating can be dicey. More so when you are going out together a lot and/or seeing each other for a while. I now know that this is something that should not be taken for granted but discussed if there is any discomfort.

How do you manage some sense of fairness about dating costs when you’ve been dating someone for a while?


Ironing Out Dating WrinklesExplore other uncomfortable situations in Ironing Out Dating Wrinkles: Work Through Challenges Without Getting Steamed. Get your copy today.

About Yury Zvyagolskiy

Yury Zvyagolskiy
In almost all American movies there is a bad guy who is usually Russian and his name is Yury. If the bad guy is not from Russia, his last name usually starts with Z. So here I am - Yury Z. My specialty is personal effectiveness. I am an expert in goal achievement, personal effectiveness, relationships and effective thinking.

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